Chesterton Holidays from AU$1,839

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Your Chesterton Holiday

Planning your next big travel adventure is easy with a Chesterton holiday package. The neighbourhood of Miller Beach, which is good for nature, makes a terrific base to uncover the treasures of this city. Want to start exploring your surroundings? Indiana Dunes National Park, Indiana Dunes State Park and Portage Lakefront Beach are just three of the top-rated places to visit during a trip to Chesterton. Whoever you're escaping with and whatever your bank balance, your dream Chesterton holiday is only clicks away with Expedia.

The Latest Chesterton Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was AU$3,931, price is now AU$1,839 per person
AU$1,839
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,617 reviews)
Comfortable room & bathroom. Everything was fine

Reviewed on 19 Aug. 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$4,291, price is now AU$1,977 per person
AU$1,977
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Modern comfortable hotel in a good location close to downtown parks and museums Friendly helpful staff Many good restaurants nearby

Reviewed on 19 Aug. 2025

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

Bluegreen Vacations Hotel Blake, Ascend Resort Collection

4 out of 5
Downtown Chicago
Price was AU$4,182, price is now AU$1,929 per person
AU$1,929
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
9.6/10 Exceptional! (1,005 reviews)
The staff, location and comfort of the bed makes this one of better places to stay in Chicago. We loved every moment of our stay! Highly recommend this beautiful hotel to stay within walking distance of all the things, but to be far away enough from the crowded areas. Also highly recommend the wine and beer bar up the street! It has great outdoor seating and great vibes overall.

Reviewed on 19 Aug. 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was AU$4,232, price is now AU$1,966 per person
AU$1,966
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Check in and out was seamless! Got excellent help with bags and access to amenities! Great location it was about a 9 min walk to Riverwalk, Hop on Bus; felt safe and area was clean

Reviewed on 18 Aug. 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was AU$3,992, price is now AU$1,855 per person
AU$1,855
per person
22 Oct - 25 Oct
found 1 day ago
Return flight included
Adelaide (ADL) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Great spot, good location, nice rooms.

Reviewed on 20 Aug. 2025

Chesterton Holiday

Chesterton Essential Information

Language
English
Currency
U.S dollars
Population
13,400
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Indiana Dunes National Park, Indiana Dunes State Park and Lake View Beach

Our pick of the best Chesterton Hotel Deals

Spring House Inn

Spring House Inn

2.5 out of 5
303 N Mineral Springs Rd, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 2 Sept to 3 Sept
AU$196
2 Sept - 3 Sept
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"I absolutely loved this place. Very quaint, loved the decor. Set in the woods. Very cool Pizzeria Uno next door, which used to be a speak easy. Staff is friendly and helpful. I wish we had more time here, but this was a quick overnight stop on a long road trip. Rooms were comfortable and good size, ..."

Reviewed on 16 Aug. 2025

Spring House Inn
Best Western Indian Oak

Best Western Indian Oak

2.5 out of 5
558 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is AU$176 per night from 1 Sept to 2 Sept
AU$176
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,005 reviews)
"The property was clean. Staff was friendly and helpful."

Reviewed on 17 Aug. 2025

Best Western Indian Oak
Waterbird Lakeside Inn

Waterbird Lakeside Inn

2 out of 5
556 Indian Boundary Road, Chesterton, IN
Fully refundableReserve now, pay when you stay
The price is AU$431 per night from 23 Aug to 24 Aug
AU$431
23 Aug - 24 Aug
includes taxes & fees
8/10 Very Good! (909 reviews)
"Overall the stay was decent. The lady at the front desk was not overly friendly. If you want cleaning services you must request it, otherwise they won’t do it. The room and building felt a little outdated, but overall, clean"

Reviewed on 17 Aug. 2025

Waterbird Lakeside Inn
See all 1,374 properties in Chesterton
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Chesterton

Indiana Dunes State Park showing general coastal views and a sandy beach as well as a family

Indiana Dunes State Park

The southern shores of Lake Michigan consist of a stunning dune landscape, which is ideal for hiking, camping, bird-watching, picnicking and swimming.

Indiana Dunes State Park

Lustron House

Find out about the history of Chesterton with a stop at Lustron House. Wander the area's beautiful beaches or simply enjoy one of its cosy cafes.

Lustron House

Frequently asked questions

How much does a Chesterton holiday package cost?
You can grab a holiday package to this top destination from AU$1,839 on Expedia. However, how much your holiday to Chesterton costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Chesterton?
If you're looking to book a cheap Chesterton holiday package, consider planning a trip in December, January and February. You'll typically find lower prices on hotels and flights during these months — perfect for a budget-friendly getaway.
How many days is enough for Chesterton?
Typically, a few days is enough for a Chesterton holiday. With a carefully crafted itinerary, you can see all the top attractions like Coffee Creek Watershed Conservancy Preserve, as well as explore some hidden gems along the way.
Is it worth booking a holiday package to Chesterton?
From cool attractions such as Coffee Creek Watershed Conservancy Preserve and Lustron House to its terrific golfing, a Chesterton holiday guarantees an unforgettable adventure. With so much to see and do, find out for yourself why Chesterton is such a good holiday destination.
How to find the best Chesterton package deals?
Landing a cheap Chesterton package deal is easy with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tweak your search by "Amenities," "Property type," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Chesterton package deals. Want a simple trick to score even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book a Chesterton holiday as a package?
An Expedia holiday package could land you significant savings when compared to booking stays and flights individually. Better still, you can personalise your Chesterton trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Chesterton?
If you're considering an impromptu Chesterton holiday, browse our last-minute deals that can be booked up to one week before you go. Don't want to leave things to the last minute? You can score sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Chesterton?

  1. Choose when to go: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Chesterton.
  2. Set a budget: Consider expenses such as food, flights and transportation when working out how much to save for your trip to Chesterton. Then, pick a property that matches your budget, whether that's a low-cost stay or a lavish retreat.
  3. Determine how many days away: Start by listing all the activities and sights you'd like to experience in Chesterton. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your airfare and accommodation: After you've nailed down your dates and duration, lock in the right Chesterton holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.